Ethanol → HCID 67413298, compound

HRID 1036420Notes

Reaction equation

HRID 1036420 reaction equation
[CH2:1]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH:2]1[O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH:18]=[C:17]([C@:22]1([CH3:28])[CH2:26][O:25]C(=O)[NH:23]1)[CH:16]=[CH:15]2.C(O)C.O.[OH-].[Li+].O>>[NH2:23][C@@:22]([C:17]1[CH:16]=[CH:15][C:14]2[C:19](=[CH:20][CH:21]=[C:12]([O:11][CH:2]3[CH2:3][CH2:4][CH:5]4[CH:10]([CH2:9][CH2:8][CH2:7][CH2:6]4)[CH2:1]3)[CH:13]=2)[CH:18]=1)([CH3:28])[CH2:26][OH:25]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67413822HCID 67413822, compound

Product 1

HCID 67413298HCID 67413298, compoundYield 2.3%

Conditions

Temperature
80 °C

Procedure

(R)-4-[6-(Decahydro-naphthalen-2-yloxy)-naphthalen-2-yl]-4-methyl-oxazolidin-2-one (200 mg, 0.0005 mol) was dissolved in ethanol (2.2 g, 0.049 mol) and treated with 4.2 M lithium hydroxide, monohydrate in water (2.1 mL, 0.0090 mol). The mixture was then heated to 80° C. overnight. The reaction was then cooled to room temperature and quenched with 1 N HCl. The reaction was then diluted with water and white solid formed. Solid was removed via filtration and dried overnight on filter to give 4 mg the desired product as a white solid (2%). ESI-MS: 337 (M−16)+. 1H NMR (400 MHz, DMSO-d6) δ=7.11-6.92 (m, 3H), 6.75-6.64 (m, 1H), 6.48-6.29 (m, 2H), 3.74-3.58 (m, 1H), 3.20-2.95 (m, 2 H), 1.21-0.96 (s, 22H).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. customquenched with 1 N HCl
  3. additionThe reaction was then diluted with water and white solid
  4. customformed
  5. customSolid was removed via filtration
  6. customdried overnight
  7. filtrationon filter

Sources & evidence

ORD record
ord-99da51c48576430da4c6619eea7346d2
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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